TuscanyArea guide

Villas in Montepulciano, Tuscany

A hill town known for Vino Nobile, with vineyards and a convenient base for exploring the Val d’Orcia.

1 villa in Montepulciano in our collection, sleeping 12 guests; every one has a private pool and 1 list a heated pool. A private chef can be arranged at every villa.

1 villa in the collection

Villas in Montepulciano

The whole collection

1 villas

Villa San Bartolomeo, a villa in Montepulciano, Tuscany
Historic Estate01
Villa San Bartolomeo

Montepulciano · 12 guests · 6 bedrooms

From €13,125 / week

Spa · Infinity pool

The only villa in the Val d'Orcia with a private wellness centre of its own: an indoor pool heated to 38°C with hydromassage…

On Montepulciano

Montepulciano,
from Smaranda.

Montepulciano is the Renaissance hill town at the meeting point of the Val d'Orcia and the Val di Chiana, and the home of Vino Nobile, the Sangiovese that considered itself noble centuries before the marketing age. The town's distinctive habit is vertical: a single corso climbs from Porta al Prato to the Piazza Grande at the top, and the great wine cellars are dug directly beneath the palazzi, so that a walk up the street passes over barrel vaults without knowing it.

For our guests the town is one of the two anchor visits of a Val d'Orcia week, about forty minutes from the Castiglion del Bosco estate with Pienza conveniently on the road between. The historic cellars, Contucci and De Ricci above all, can be wandered into without an appointment; a proper seated tasting is worth booking a day or two ahead, and during the vendemmia weeks we arrange these as part of the week alongside the wine tours we run across both valleys.

The Bravìo, San Biagio and the Evening

On the last Sunday of August the town runs the Bravìo delle Botti, pairs of pushers racing eighty-kilo wine barrels up the full length of the corso to the Piazza Grande, contrada flags and drummers filling the week before. Below the walls, Sangallo's Tempio di San Biagio is the Renaissance set piece, honey-coloured travertine alone among cypresses, best in the last hour of light. The town at seven in the evening, when the day visitors have gone and the enoteche put tables out on the stones, is the argument for staying in the countryside nearby rather than passing through.

When to come

May, June, September and October. Late September adds the vendemmia; the Bravìo closes August with the town at its most alive. Winter is quiet and many cellars keep short hours.

Towns worth knowing

Montepulciano
The corso climb, the underground cellars, Piazza Grande at the summit.
Monticchiello
Walled village on the Pienza road; its summer Teatro Povero is played by the villagers themselves.
Chianciano Terme
The old spa town; faded grandeur and serious thermal water.
Torrita di Siena
Workaday Valdichiana town with one of the area's best Sunday markets.

Best for

  • Wine-led weeks in the Val d'Orcia
  • Guests pairing Brunello and Vino Nobile country
  • An evening town after villa afternoons
  • The Bravìo, for late-August stays

Plan your stay

Plan a day in town with our guide to things to do in Montepulciano. If your party will be based at a larger villa, our family villa planning guide covers the bedroom and shared-space questions to settle before booking.

Practicalities

The centre is a ZTL; park at the Sant'Agnese lot by Porta al Prato and walk up. From Castiglion del Bosco allow forty minutes; the nearest rail is Chiusi-Chianciano Terme, twenty minutes down the hill.

Frequently asked

How many villas do you have in Montepulciano?
1: Villa San Bartolomeo (sleeps 12).
Which villas in Montepulciano have a private pool?
1 of 1: Villa San Bartolomeo (25-metre outdoor infinity pool with panoramic lounge, plus an indoor…). Tell us your dates and we will confirm which are free.
When are the pools open in Montepulciano?
Most villa pools in Tuscany open from May to late September; heated pools usually extend the season from April into October. 1 of the villas here list a heated pool (Villa San Bartolomeo); heating can carry an extra charge, so we confirm it for your dates. Opening dates are set by each villa. In high season villas rent Saturday to Saturday.
Which villas in Montepulciano suit large groups?
1 sleep 12 or more: Villa San Bartolomeo (sleeps 12, 6 bedrooms). For a celebration, ask about seated dining for the whole group and whether outside guests are allowed.
Is Montepulciano the same as Montepulciano d'Abruzzo?
No, and the confusion flatters neither. This Montepulciano is a Tuscan town making Vino Nobile from Sangiovese; Montepulciano d'Abruzzo is a grape variety grown four hundred kilometres east. The town came first by several centuries.
Do the Montepulciano wine cellars need booking?
Wandering into the historic cellars under the town costs nothing and needs no appointment. Seated tastings are worth booking a day or two ahead, and during the harvest weeks of late September the producers' calendars fill.

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